Tony Bennett and Lady Gaga, The Lady is a Tramp
Bennett is a classy, dapper old-school guy. Gaga is, well, a little monster. But strip away the wigs, meat dresses and makeup, and her voice is actually pretty jazzy and really complements his on this classic standard.
Janet Jackson and Carly Simon, Son of a Gun (I Betcha Think This Song is About You)
Jackson used a sample of Simon’s hit song “You’re So Vain” for this cut from her 2001 album All For You. But when she sent the song to Simon to get her permission to use the sample, Simon just sent it back with new vocals…including a part with Simon rapping. Somehow, it works.
Stevie Wonder and Paul McCartney, Ebony & Ivory
Despite reaching number one (for seven weeks!) on the charts in 1982, this song has appeared on quite a few ‘Worst Songs of All-Time” lists and has been parodied on everything from Arrested Development to Late Night with Jimmy Fallon.
Gwyneth Paltrow and Huey Lewis, Cruisin’
Back in the day (before she was a GOOP-y lifestyle expert), Paltrow was a movie star and recorded this remake with ‘80s rocker Huey Lewis for the 2000 film Duets. The song actually went number one…in Australia!
Nelly and Tim McGraw, Over and Over
This hip-hop-meets-country ballad reached number three on the Billboard charts. Warning: The catchy song will probably get stuck in your head for the rest of the afternoon.
Snoop Dogg and Willie Nelson, Superman
We know Snoop and Nelson have at least one thing in common…and on this song, the pair teams up for a country-tinged ditty that appeared on Snoop’s Doggumentary album. The two have collaborated numerous times, including on Willie’s 2012 track “Roll Me Up and Smoke Me When I Die.”
R. Kelly and Celine Dion, I’m Your Angel
This 1998 single is from Kelly’s “I Believe I Can Fly” era and just when Dion was riding high from her Titanic hit “My Heart Will Go On.” So, considering where each performer was at that point, this song is just as cheesy and inspirational as you’d imagine.
Nicole Kidman and Robbie Williams, Somethin’ Stupid
This classic song (best known as a duet between Frank Sinatra and his daughter Nancy) got an update in 2001 on Williams’s album Swing When You’re Winning. We already knew Kidman could sing, thanks to the movie Moulin Rouge, and are a bit surprised she hasn’t made more recordings.
The Flaming Lips and Ke$ha, 2012 (You Must Be Upgraded)
Rumor has it that Flaming Lips singer Wayne Coyne enjoyed working with Ke$ha so much that the band was planning to make a whole album—called Lip$ha—together. But the project was mysteriously scrapped late last year.
Timbaland and Elton John, 2 Man Show
They’re both master collaborators, so it makes perfect sense that they combined powers for this piano-riff-meets-hip-hop jingle. The vocals belong mostly to Timbo, but Elton’s mastery on the ivory keys brings 2007’s Shock Value to a satisfying end. Elton has had some wild collaborations in his day—Eminem, anyone?—but this is one of our subtler favorites.